This invention is related to the field of compounds having fungicidal activity and processes to make and use such compounds.
Our history is riddled with outbreaks of fungal diseases that have caused widespread human suffering. One need look no further than the Irish potato famine, which occurred from 1845 to 1860, where an estimated 1,000,000 people died, and an estimated 1,500,000 people emigrated, to see the effects of a fungal disease. Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield and the quality of the crop and consequently, increase the value of the crop. In most situations, the increase in value of the crop is worth at least three times the cost of the use of the fungicide. However, no one fungicide is useful in all situations. Consequently, research is being conducted to produce fungicides that are safer, that have better performance, that are easier to use, and that cost less. In light of the above, the inventors provide this invention.
It is an object of this invention to provide compounds that have fungicidal activity. It is an object of this invention to provide processes that produce compounds that have fungicidal activity. It is an object of this invention to provide processes that use compounds that have fungicidal activity. In accordance with this invention, processes to make and processes to use compounds having a general formula according to formula one, and said compounds are provided. While all the compounds of this invention have fungicidal activity, certain classes of compounds may be preferred for reasons such as, for example, greater efficacy or ease of synthesis.
Throughout this document, all temperatures are given in degrees Celsius and all percentages are weight percentages, except for percent yields which are mole percentages, unless otherwise stated. The term xe2x80x9calkylxe2x80x9d, xe2x80x9calkenylxe2x80x9d, or xe2x80x9calkynylxe2x80x9d refers to an unbranched, or branched, chain carbon group. The term xe2x80x9calkoxyxe2x80x9d refers to an unbranched, or branched, chain alkoxy group. The term xe2x80x9chaloalkylxe2x80x9d refers to an unbranched, or branched, alkyl group substituted with one or more halo atoms, defined as F, Cl, Br, and I. The term xe2x80x9chaloalkoxyxe2x80x9d refers to an unbranched, or branched, chain alkoxy group substituted with one or more halo atoms. The term xe2x80x9calkoxylalkylxe2x80x9d refers to an unbranched, or branched, chain alkyl group substituted with one or more alkoxy groups. The term xe2x80x9calkoxyalkoxyxe2x80x9d refers to an unbranched, or branched, chain alkoxy group substituted with one or more alkoxy groups. The term xe2x80x9carylxe2x80x9d refers to a phenyl or naphthyl group. The term xe2x80x9cMexe2x80x9d refers to a methyl group. The term xe2x80x9cEtxe2x80x9d refers to an ethyl group. The term xe2x80x9cPrxe2x80x9d refers to a propyl group. The term xe2x80x9cBuxe2x80x9d refers to a butyl group. The term xe2x80x9cEtOAcxe2x80x9d refers to ethyl acetate. The term xe2x80x9cppmxe2x80x9d refers to parts per million. The term, xe2x80x9cpsixe2x80x9d refers to pounds per square inch.
Heteroaryl is defined by the following Formula Two 
wherein 2A represents a 5- or 6-membered ring and 2B represents a 9- or 10-membered fused bicyclic ring in which each of X1-X5 is independently a bond, O, S, NR7, N, or CR, where R is selected from the group consisting of halo, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, C1-4 alkoxyalkyl, C1-4 alkoxyalkoxy, CN, NO2, OH, SCN, C(xe2x95x90O)R6, C(xe2x95x90NR6)R6, S(On)R6 where n=0, 1 or 2, aryl, aryloxy, heteroaryl, and heteroaryloxy, and where no more than one of X1-X5 is O, S, or NR7, no more than one of X1-X5 is a bond, when any one of X1-X5 is S, O or NR7, one of the adjacent X1-X5 must represent a bond; and at least one of X1-X5 must be O, S, NR7 or N.
Examples of such heteroaryls are pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, indolyl, isoindolyl, indazolyl, thienyl, benzothienyl, furanyl, benzofuranyl, thiazolyl, benzothiazolyl, isothiazolyl, benzoisothiazolyls, oxazolyl, benzoxazolyl, isoxazolyl, and benzoisoxazolyl.